Activate the Yeast: In a small bowl, combine warm milk and 1 tablespoon of sugar. Sprinkle yeast and let it sit until frothy.
Prepare the Dough: Mix flour, remaining sugar, and salt. Add yeast mixture, eggs, vanilla, and butter. Knead until smooth.
First Rise: Place dough in an oiled bowl, cover, and let rise until doubled (1-2 hours).
Incorporate Chocolate Chips: Punch down the dough and knead in chocolate chips.
Shape and Braid the Dough: Divide into three strands, braid, and place on a baking sheet.
Second Rise: Cover and let rise for 30-45 minutes.
Bake to Perfection: Preheat oven and brush with egg wash. Bake until golden brown.